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Vacation rentals in São Mateus da Calheta

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in São Mateus da Calheta

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Angra do Heroismo

4.9 out of 5 average rating, 41 reviews

Ocean - Casa Sao Joao - 4 Star Tourist Apartments

Located in the center of Angra do Heroísmo, overlooking the ocean, Casa São João is one of the oldest, noblest and most emblematic houses in the city. Recently restored, this mid-19th century architectural jewel, accented with original stonework, arches and columns, combines the romantic charm and charisma of it’s history with the comfort, refinement and convenience of the 21st century. With a bold decor, fusing contemporary and classic elements, all spaces, from the penthouse, to the suites, to the interior garden, were designed to guarantee comfort, serenity and delight to its occupants, typically families, who can find here a home far from home. The inner peace of its nooks are just a few steps away from the bustle of the historical city or the contemplation of the sea and of Angra´s bay, given its well appointed location. It's history dates back to the 1400s, the restoration revealed and maintained the original stone work inside and out. You will be welcomed into a lovely reception area and given access to your private suite. Spacious, modern, and an architectural treasure this suite features 2 generous bedrooms 2 bathrooms and open concept lounge, dining and kitchen area. We also offer free wifi and 120V outlets for our North American guests, no transformers are required.

Oct 4 – 11

$129 per night
Guest favorite

Home in Açores

4.92 out of 5 average rating, 114 reviews

Nature Reserve With Stunning Ocean Views RRAL1117

RRAL: 1117 Entire house in private nature reserve. The property is full of protected endemic trees found only in the Azores and protected birds including Cory’s Shearwater with their curious singing just before sunrise and after sunset in residence between March and October. Natural black lava swimming pools in the village. Activities nearby include whale watching, hiking, snorkelling, scuba diving, golf, fishing, geological sites, and the Unesco World Heritage town of Angra do Heroismo.

Sep 20 – 27

$91 per night
Superhost

Cottage in Santa Bárbara

4.81 out of 5 average rating, 93 reviews

Ribeira House I - private terrace, AC & breakfast

Viva como um local nesta casa que combina uma arquitetura tradicional com um interior aconchegante, decoração moderna e totalmente equipado. É ideal para explorar a natureza e relaxar. Comece o dia com um pequeno-almoço no terraço com vista para o mar ou desfrute de um copo de vinho ao final do dia ao som da ribeira. Estamos perto de tudo (café, minimercado, restaurante - 1 minuto) mas longe o suficiente para desfrutar de uma estadia única. Perfeito para uma escapadela romântica!

Nov 11 – 18

$60 per night

Popular amenities for São Mateus da Calheta vacation rentals

Stay near São Mateus da Calheta's top sights

Restaurante Beira Mar36 locals recommend
Restaurante Quebra Mar5 locals recommend
Negrito7 locals recommend
Supermercado Guarita5 locals recommend
Adega de São Mateus9 locals recommend
Giant Expeditions Azores4 locals recommend

Other great vacation rentals in São Mateus da Calheta

Guest favorite

Townhouse in Angra do Heroísmo

4.92 out of 5 average rating, 26 reviews

Breathe Nature - Salga Bay House AL 1199

Sep 21 – 28

$103 per night
Guest favorite

Home in Açores

5.0 out of 5 average rating, 9 reviews

Ti Chôa_Casa do Biscoitinho

Nov 21 – 28

$95 per night
Guest favorite

Guesthouse in Santa Barbara

4.82 out of 5 average rating, 34 reviews

The Azores Homestead

Aug 29 – Sep 5

$60 per night
Guest favorite

Villa in Açores

5.0 out of 5 average rating, 11 reviews

Chalé d´Angra Guest House

Oct 14 – 21

$132 per night
Guest favorite

Villa in Terceira

5.0 out of 5 average rating, 11 reviews

Private home w/pool & sea access sleeps up to 18

Nov 22 – 29

$821 per night
Guest favorite

Windmill in Biscoitos

4.9 out of 5 average rating, 41 reviews

Old Windmill, with stunning views

Nov 18 – 25

$81 per night
Guest favorite

Tiny home in Angra do Heroísmo

5.0 out of 5 average rating, 14 reviews

Tiny House

Nov 24 – Dec 1

$55 per night
Superhost

Villa in Serreta

4.92 out of 5 average rating, 25 reviews

Cheerful villa with stunning views

Oct 19 – 26

$221 per night
Guest favorite

Townhouse in Angra do Heroísmo

4.95 out of 5 average rating, 20 reviews

Cantinho do Cantagalo - Your Atlantic Refuge

Sep 13 – 20

$117 per night
Guest favorite

Loft in Angra do Heroísmo

5.0 out of 5 average rating, 14 reviews

Villa Azul

Feb 19 – 26

$162 per night
Guest favorite

Cottage in Biscoitos

4.93 out of 5 average rating, 15 reviews

Casa do Lagar

Nov 29 – Dec 6

$119 per night
Superhost

Place to stay in Angra do Heroísmo

4.83 out of 5 average rating, 18 reviews

A Casa do Pedrinho

Jan 19 – 26

$38 per night

Quick stats about vacation rentals in São Mateus da Calheta

Total rentals

50 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

740 reviews

Nightly prices starting at

$30 before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in São Mateus da Calheta?

    Four-legged friends are welcome in São Mateus da Calheta. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do apartment rentals in São Mateus da Calheta have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in São Mateus da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in São Mateus da Calheta?

    Yes! Work meets play with ease at over 10 vacation rentals in São Mateus da Calheta featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in São Mateus da Calheta?

    Experience the best of São Mateus da Calheta with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there São Mateus da Calheta vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in São Mateus da Calheta, available on Airbnb. Make a splash and soak up the sun in style!

  • What are the most popular amenities for Apartment Rentals in São Mateus da Calheta?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in São Mateus da Calheta?

    São Mateus da Calheta has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in São Mateus da Calheta have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in São Mateus da Calheta. Enjoy a tailored experience with all the comforts you desire.

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